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Special Issue "Bioactive Compounds from Marine Microbes II, 2017"

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: 31 July 2018

Special Issue Editors

Guest Editor
Prof. Vítor Vasconcelos

1. CIIMAR – Interdisciplinary Centre of Marine and Environmental Research, Matosinhos, Portugal
2. Department of Biology, Faculty of Sciences, Porto University, Porto 4069-007, Portugal
Website | E-Mail
Phone: +351 223401814
Fax: +351 223380609
Interests: blue-biotechnology; emerging marine toxins; bioassay-guided approach; cyanobacteria bioactive compounds
Co-Guest Editor
Dr. Pedro Leão

Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos, s/n, 4450-208 Matosinhos, Portugal
E-Mail
Interests: chemical ecology; secondary metabolites; biosynthesis; cyanobacteria; structural elucidation

Special Issue Information

Dear Colleagues,

Arguably nature’s most talented chemists, microbes, have contributed to human medicine with many small molecules that are used to treat infection, cancer and many other diseases. The marine environment harbors a multiplicity of microorganisms, much of which yet to be catalogued. This remarkable biodiversity naturally translates into chemical diversity—we currently recognize that a large fraction of marine natural products has either been isolated from microbes or, despite being obtained from collections of macroorganisms, has a microbial origin. Plenty of chemistry remains to be discovered from the marine microbiota and opportunities for unearthing important biological activity abound.

This Special Issue will highlight: the isolation, structural elucidation and biological activity evaluation of unprecedented compounds of marine microbial origin; the potential of underexplored marine microbial groups for the production of bioactive small molecules; as well as the microbial biogenesis of novel or previously known marine natural products obtained from non-microbial sources.

Prof. Dr. Vítor Vasconcelos
Dr. Pedro Leão
Guest Editors

Keywords

  • Secondary metabolites
  • Natural products
  • Structure elucidation
  • Bioactivity
  • Biogenetic origin

Published Papers (11 papers)

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Research

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Open AccessArticle Two New Diketomorpholine Derivatives and a New Highly Conjugated Ergostane-Type Steroid from the Marine Algal-Derived Endophytic Fungus Aspergillus alabamensis EN-547
Mar. Drugs 2018, 16(4), 114; doi:10.3390/md16040114
Received: 25 February 2018 / Revised: 27 March 2018 / Accepted: 30 March 2018 / Published: 31 March 2018
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Abstract
Chemical investigation of the marine algal-derived endophytic fungus Aspergillus alabamensis EN-547 resulted in the isolation of 4-epi-seco-shornephine A methyl ester (1) and 4-epi-seco-shornephine A carboxylic acid (2), two new secondary metabolites
[...] Read more.
Chemical investigation of the marine algal-derived endophytic fungus Aspergillus alabamensis EN-547 resulted in the isolation of 4-epi-seco-shornephine A methyl ester (1) and 4-epi-seco-shornephine A carboxylic acid (2), two new secondary metabolites having a rare diketomorpholine motif, and 28-acetoxy-12β,15α,25-trihydroxyergosta-4,6,8(14),22-tetraen-3-one (3), a new highly conjugated ergostane-type steroid, together with four known metabolites (47). Their chemical structures were elucidated by detailed analysis of their NMR spectra, ECDs, HRESIMS, optical rotation, and X-ray crystallographic data, and by comparison with literature data as well. The antimicrobial activities of compounds 17 were evaluated. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle Chlorinated Azaphilone Pigments with Antimicrobial and Cytotoxic Activities Isolated from the Deep Sea Derived Fungus Chaetomium sp. NA-S01-R1
Mar. Drugs 2018, 16(2), 61; doi:10.3390/md16020061
Received: 13 January 2018 / Revised: 30 January 2018 / Accepted: 10 February 2018 / Published: 13 February 2018
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Abstract
Four novel compounds, chaephilone C (1), chaetoviridides A–C (24), were obtained from the culture of a deep sea derived fungus Chaetomium sp. NA-S01-R1, together with four known compounds—chaetoviridin A (5), chaetoviridine E (6),
[...] Read more.
Four novel compounds, chaephilone C (1), chaetoviridides A–C (24), were obtained from the culture of a deep sea derived fungus Chaetomium sp. NA-S01-R1, together with four known compounds—chaetoviridin A (5), chaetoviridine E (6), chaetomugilin D (7) and cochliodone A (8). Their structures, including absolute configurations, were assigned based on NMR, MS and time-dependent density functional theory (TD-DFT) ECD calculations. A plausible biogenetic pathway for compounds 13 was proposed. Compounds 2 and 3 exhibited antibacterial activities against Vibrio rotiferianus and Vibrio vulnificus. Compounds 1, 3 and 4 displayed similar anti-methicillin resistant Staphylococcus aureus (anti-MRSA) activities in comparison to chloramphenicol. Compound 2 showed the most potent cytotoxic activities towards the Hep G2 cell and compounds 1 and 3 demonstrated relatively stronger cytotoxic activities than the other compounds against the HeLa cell. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle Anti-Phytopathogenic and Cytotoxic Activities of Crude Extracts and Secondary Metabolites of Marine-Derived Fungi
Mar. Drugs 2018, 16(1), 36; doi:10.3390/md16010036
Received: 30 November 2017 / Revised: 8 January 2018 / Accepted: 15 January 2018 / Published: 18 January 2018
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Abstract
Thirty-one isolates belonging to eight genera in seven orders were identified from 141 strains that were isolated from several marine plants. Alternaria sp. and Fusarium sp. were found to be the predominant fungi. Evaluation of the anti-phytopathogenic bacterial and fungal activities, as well
[...] Read more.
Thirty-one isolates belonging to eight genera in seven orders were identified from 141 strains that were isolated from several marine plants. Alternaria sp. and Fusarium sp. were found to be the predominant fungi. Evaluation of the anti-phytopathogenic bacterial and fungal activities, as well as the cytotoxicity of these 31 extracts, revealed that most of them displayed different levels of bioactivities. Due to their interesting bioactivities, two fungal strains—Fusarium equiseti (P18) and Alternaria sp. (P8)—were selected for chemical investigation and compounds 14 were obtained. The structure of 1 was elucidated by 1D and 2D NMR analysis, as well as high-resolution electrospray ionization mass spectroscopy (HRESIMS), and the absolute configuration of its stereogenic carbon (C-11) was established by comparison of the experimental and calculated electronic circular-dichroism (ECD) spectra. Moreover, alterperylenol (4) exhibited antibacterial activity against Clavibacter michiganensis with a minimum inhibitory concentration (MIC) of 1.95 μg/mL, which was 2-fold stronger than that of streptomycin sulfate. Additionally, an antibacterial mechanism study revealed that 4 caused membrane hyperpolarization without evidence of destruction of cell membrane integrity. Furthermore, stemphyperylenol (3) displayed potent antifungal activity against Pestallozzia theae and Alternaria brassicicola with MIC values equal to those of carbendazim. The cytotoxicity of 1 and 2 against human lung carcinoma (A-549), human cervical carcinoma (HeLa), and human hepatoma (HepG2) cell lines were also evaluated. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitory Activity of Plastoquinones from Marine Brown Alga Sargassum serratifolium
Mar. Drugs 2017, 15(12), 368; doi:10.3390/md15120368
Received: 25 October 2017 / Revised: 18 November 2017 / Accepted: 27 November 2017 / Published: 1 December 2017
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Abstract
Sargassum serratifolium C. Agardh (Phaeophyceae, Fucales) is a marine brown alga that belongs to the family Sargassaceae. It is widely distributed throughout coastal areas of Korea and Japan. S. serratifolium has been found to contain high concentrations of plastoquinones, which have strong anti-cancer,
[...] Read more.
Sargassum serratifolium C. Agardh (Phaeophyceae, Fucales) is a marine brown alga that belongs to the family Sargassaceae. It is widely distributed throughout coastal areas of Korea and Japan. S. serratifolium has been found to contain high concentrations of plastoquinones, which have strong anti-cancer, anti-inflammatory, antioxidant, and neuroprotective activity. This study aims to investigate the anti-diabetic activity of S. serratifolium and its major constituents through inhibition of protein tyrosine phosphatase 1B (PTP1B), α-glucosidase, and ONOO-mediated albumin nitration. S. serratifolium ethanolic extract and fractions exhibited broad PTP1B and α-glucosidase inhibitory activity (IC50, 1.83~7.04 and 3.16~24.16 µg/mL for PTP1B and α-glucosidase, respectively). In an attempt to identify bioactive compounds, three plastoquinones (sargahydroquinoic acid, sargachromenol and sargaquinoic acid) were isolated from the active n-hexane fraction of S. serratifolium. All three plastoquinones exhibited dose-dependent inhibitory activity against PTP1B in the IC50 range of 5.14–14.15 µM, while sargachromenol and sargaquinoic acid showed dose-dependent inhibitory activity against α-glucosidase (IC50 42.41 ± 3.09 and 96.17 ± 3.48 µM, respectively). In the kinetic study of PTP1B enzyme inhibition, sargahydroquinoic acid and sargaquinoic acid led to mixed-type inhibition, whereas sargachromenol displayed noncompetitive-type inhibition. Moreover, plastoquinones dose-dependently inhibited ONOO-mediated albumin nitration. Docking simulations of these plastoquinones demonstrated negative binding energies and close proximity to residues in the binding pocket of PTP1B and α-glucosidase, indicating that these plastoquinones have high affinity and tight binding capacity towards the active site of the enzymes. These results demonstrate that S. serratifolium and its major plastoquinones may have the potential as functional food ingredients for the prevention and treatment of type 2 diabetes. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle Lactones from the Sponge-Derived Fungus Talaromyces rugulosus
Mar. Drugs 2017, 15(11), 359; doi:10.3390/md15110359
Received: 12 October 2017 / Revised: 6 November 2017 / Accepted: 9 November 2017 / Published: 14 November 2017
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Abstract
The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (15), seven (3S)-resorcylide derivatives (612), two butenolide-resorcylide dimers
[...] Read more.
The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (15), seven (3S)-resorcylide derivatives (612), two butenolide-resorcylide dimers (13 and 14), and three dihydroisocoumarins (1517). Among them, fourteen compounds (13, 616) are new natural products. The structures of the isolated compounds were elucidated by 1D and 2D NMR (Nuclear Magnetic Resonance) spectroscopy as well as by ESI-HRMS (ElectroSpray Ionization-High Resolution Mass Spectrometry). TDDFT-ECD (Time-Dependent Density Functional Theory-Electronic Circular Dichroism) calculations were performed to determine the absolute configurations of chiral compounds. The butenolide-resorcylide dimers talarodilactones A and B (13 and 14) exhibited potent cytotoxicity against the L5178Y murine lymphoma cell line with IC50 values of 3.9 and 1.3 µM, respectively. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle Biological and Chemical Diversity of Bacteria Associated with a Marine Flatworm
Mar. Drugs 2017, 15(9), 281; doi:10.3390/md15090281
Received: 20 July 2017 / Revised: 21 August 2017 / Accepted: 29 August 2017 / Published: 1 September 2017
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Abstract
The aim of this research is to explore the biological and chemical diversity of bacteria associated with a marine flatworm Paraplanocera sp., and to discover the bioactive metabolites from culturable strains. A total of 141 strains of bacteria including 45 strains of actinomycetes
[...] Read more.
The aim of this research is to explore the biological and chemical diversity of bacteria associated with a marine flatworm Paraplanocera sp., and to discover the bioactive metabolites from culturable strains. A total of 141 strains of bacteria including 45 strains of actinomycetes and 96 strains of other bacteria were isolated, identified and fermented on a small scale. Bioactive screening (antibacterial and cytotoxic activities) and chemical screening (ultra-performance liquid chromatography–mass spectrometry (UPLC-MS)) yielded several target bacterial strains. Among these strains, the ethyl acetate (EA) crude extract of Streptomyces sp. XY-FW47 fermentation broth showed strong antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC43300 (MRSA ATCC43300) and potent cytotoxic effects on HeLa cells. The UPLC-MS spectral analysis of the crude extract indicated that the strain XY-FW47 could produce a series of geldanamycins (GMs). One new geldanamycin (GM) analog, 4,5-dihydro-17-O-demethylgeldanamycin (1), and three known GMs (2–4) were obtained. All of these compounds were tested for antibacterial, cytotoxic, and antifungal activities, yet only GM (3) showed potent cytotoxic (HeLa cells, EC50 = 1.12 μg/mL) and antifungal (Setosphaeria turcica MIC = 2.40 μg/mL) activities. Their structure–activity relationship (SAR) was also preliminarily discussed in this study. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle 5-Hydroxycyclopenicillone, a New β-Amyloid Fibrillization Inhibitor from a Sponge-Derived Fungus Trichoderma sp. HPQJ-34
Mar. Drugs 2017, 15(8), 260; doi:10.3390/md15080260
Received: 17 May 2017 / Accepted: 16 August 2017 / Published: 19 August 2017
Cited by 3 | PDF Full-text (3432 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Abstract: A new cyclopentenone, 5-hydroxycyclopeni cillone (1), was isolated together with three known compounds, ar-turmerone (2), citreoisocoumarin (3), and 6-O-methyl-citreoisocoumarin (4), from a culture of the sponge-derived fungus Trichoderma sp. HPQJ-34. The
[...] Read more.
Abstract: A new cyclopentenone, 5-hydroxycyclopeni cillone (1), was isolated together with three known compounds, ar-turmerone (2), citreoisocoumarin (3), and 6-O-methyl-citreoisocoumarin (4), from a culture of the sponge-derived fungus Trichoderma sp. HPQJ-34. The structures of 14 were characterized using comprehensive spectroscopic analyses. The absolute configuration of 1 was determined by comparison of electronic circular dichroism (ECD) spectra with literature values used for the reported analogue, cyclopenicillone (5), which was not isolated in this research. Compound 1 was shown to scavenge 2,2-diphenyl-1-picrylhydrazyl free radicals, and decrease β-amyloid (Aβ) fibrillization in vitro. Moreover, 1 significantly reduced H2O2-induced neurotoxicity in SH-SY5Y cells. These findings suggested that compound 1, a newly discovered cyclopentenone, has moderate anti-oxidative, anti-Aβ fibrillization properties and neuroprotective effects, and might be a good free radical scavenger. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle A Novel Benzoquinone Compound Isolated from Deep-Sea Hydrothermal Vent Triggers Apoptosis of Tumor Cells
Mar. Drugs 2017, 15(7), 200; doi:10.3390/md15070200
Received: 16 April 2017 / Revised: 2 June 2017 / Accepted: 16 June 2017 / Published: 26 June 2017
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Abstract
Microorganisms are important sources for screening bioactive natural products. However, natural products from deep-sea microbes have not been extensively explored. In this study, the metabolites of bacteriophage GVE2 -infected (Geobacillus sp. E263 virus) thermophilic bacterium Geobacillus sp. E263, which was isolated from
[...] Read more.
Microorganisms are important sources for screening bioactive natural products. However, natural products from deep-sea microbes have not been extensively explored. In this study, the metabolites of bacteriophage GVE2 -infected (Geobacillus sp. E263 virus) thermophilic bacterium Geobacillus sp. E263, which was isolated from a deep-sea hydrothermal vent, were characterized. A novel quinoid compound, which had anti-tumor activity, was isolated from the phage-challenged thermophile. The chemical structure analysis showed that this novel quinoid compound was 2-amino-6-hydroxy-[1,4]-benzoquinone. The results indicated that 2-amino-6-hydroxy-[1,4]-benzoquinone and its two derivatives could trigger apoptosis of gastric cancer cells and breast cancer cells by inducing the accumulation of intracellular reactive oxygen species. Therefore, our study highlighted that the metabolites from the phage-challenged deep-sea microbes might be a kind of promising sources for anti-tumor drug discovery, because of the similarity of metabolic disorder between bacteriophage-infected microbes and tumor cells. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle Effect of Supercritical Carbon Dioxide Extraction Parameters on the Biological Activities and Metabolites Present in Extracts from Arthrospira platensis
Mar. Drugs 2017, 15(6), 174; doi:10.3390/md15060174
Received: 23 February 2017 / Revised: 8 May 2017 / Accepted: 6 June 2017 / Published: 12 June 2017
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Abstract
Arthrospira platensis was used to obtain functional extracts through supercritical carbon dioxide extraction (SFE-CO2). Pressure (P), temperature (T), co-solvent (CX), static extraction (SX), dispersant (Di) and dynamic extraction (DX) were evaluated as process parameters through a Plackett–Burman design. The maximum extract
[...] Read more.
Arthrospira platensis was used to obtain functional extracts through supercritical carbon dioxide extraction (SFE-CO2). Pressure (P), temperature (T), co-solvent (CX), static extraction (SX), dispersant (Di) and dynamic extraction (DX) were evaluated as process parameters through a Plackett–Burman design. The maximum extract yield obtained was 7.48 ± 0.15% w/w. The maximum contents of bioactive metabolites in extracts were 0.69 ± 0.09 µg/g of riboflavin, 5.49 ± 0.10 µg/g of α-tocopherol, 524.46 ± 0.10 µg/g of β-carotene, 1.44 ± 0.10 µg/g of lutein and 32.11 ± 0.12 mg/g of fatty acids with 39.38% of palmitic acid, 20.63% of linoleic acid and 30.27% of γ-linolenic acid. A. platensis extracts had an antioxidant activity of 76.47 ± 0.71 µg GAE/g by Folin–Ciocalteu assay, 0.52 ± 0.02, 0.40 ± 0.01 and 1.47 ± 0.02 µmol TE/g by DPPH, FRAP and TEAC assays, respectively. These extracts showed antimicrobial activity against Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922 and Candida albicans ATCC 10231. Overall, co-solvent was the most significant factor for all measured effects (p < 0.05). Arthrospira platensis represents a sustainable source of bioactive compounds through SFE using the following extraction parameters P: 450 bar, CX: 11 g/min, SX: 15 min, DX: 25 min, T: 60 °C and Di: 35 g. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Open AccessArticle Three New Indole Diterpenoids from the Sea-Anemone-Derived Fungus Penicillium sp. AS-79
Mar. Drugs 2017, 15(5), 137; doi:10.3390/md15050137
Received: 8 February 2017 / Revised: 24 March 2017 / Accepted: 10 May 2017 / Published: 12 May 2017
Cited by 1 | PDF Full-text (1814 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new indolediterpenoids, namely, 22-hydroxylshearinine F (1), 6-hydroxylpaspalinine (2), and 7-O-acetylemindole SB (3), along with eight related known analogs (411), were isolated from the sea-anemone-derived fungus Penicillium sp. AS-79. The structures
[...] Read more.
Three new indolediterpenoids, namely, 22-hydroxylshearinine F (1), 6-hydroxylpaspalinine (2), and 7-O-acetylemindole SB (3), along with eight related known analogs (411), were isolated from the sea-anemone-derived fungus Penicillium sp. AS-79. The structures and relative configurations of these compounds were determined by a detailed interpretation of the spectroscopic data, and their absolute configurations were determined by ECD calculations (1 and 2) and single-crystal X-ray diffraction (3). Some of these compounds exhibited prominent activity against aquatic and human pathogenic microbes. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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Review

Jump to: Research

Open AccessReview Cytotoxic Natural Products from Marine Sponge-Derived Microorganisms
Mar. Drugs 2017, 15(3), 68; doi:10.3390/md15030068
Received: 13 December 2016 / Revised: 3 March 2017 / Accepted: 3 March 2017 / Published: 10 March 2017
Cited by 4 | PDF Full-text (3401 KB) | HTML Full-text | XML Full-text
Abstract
A growing body of evidence indicates that marine sponge-derived microbes possess the potential ability to make prolific natural products with therapeutic effects. This review for the first time provides a comprehensive overview of new cytotoxic agents from these marine microbes over the last
[...] Read more.
A growing body of evidence indicates that marine sponge-derived microbes possess the potential ability to make prolific natural products with therapeutic effects. This review for the first time provides a comprehensive overview of new cytotoxic agents from these marine microbes over the last 62 years from 1955 to 2016, which are assorted into seven types: terpenes, alkaloids, peptides, aromatics, lactones, steroids, and miscellaneous compounds. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes II, 2017)
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